Multi-step reaction with 9 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 14 h / 0 - 20 °C / Inert atmosphere
2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; tetrabutyl-ammonium chloride / dichloromethane / 19 h / pH 8.6
3.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / -78 - 20 °C / Inert atmosphere
3.2: 24 h / 20 °C / Inert atmosphere
4.1: hydrogenchloride; ethanol / tetrahydrofuran; water / 69 h / 20 °C
5.1: ozone; solvent red 19 / methanol / 0.02 h / -78 °C
5.2: 3 h / 20 °C / Inert atmosphere
5.3: 1 h / Inert atmosphere
6.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / 55 °C / Inert atmosphere; Molecular sieve
6.2: 0.5 h / 0 °C / Inert atmosphere; Molecular sieve
7.1: n-butyllithium; isopropylmagnesium bromide / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
7.2: 0.25 h / -78 °C / Inert atmosphere
7.3: 2 h / 0 °C / Inert atmosphere
8.1: N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; lithium chloride; manganese; C10H10O4*NiCl2; zirconocene dichloride / acetonitrile / 2 h / 20 °C / Inert atmosphere
9.1: N-iodo-succinimide / dichloromethane / 7.5 h / -78 °C / Inert atmosphere
With
chromium dichloride; hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; manganese; N-chloro-succinimide; N-iodo-succinimide; n-butyllithium; zirconocene dichloride; ethanol; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C10H10O4*NiCl2; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; isopropylmagnesium bromide; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; ozone; triethylamine; lithium chloride; solvent red 19;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile;
8.1: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/ol302751b